The Best Sailboat Rentals Near Me

Sail & Swim from a Luxury Sailing Yacht

We had a great experience with Captain Greg. The boat was very nice and clean, and we had a great sunset sail! Our kids loved their first sailing experience. Captain Greg even taught my 9 year old how to steer and let all 3 kiddos help with hoisting the sails. Couldn’t have asked for a better night in Chicago!

Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.

Captain Russell was incredibly hospitable and entertaining, making this Afternoon Delight even more special. On the yacht was pure bless -- sunshine, bevies, great music and stunning Lake Michigan views. Plus there's a huge Yeti Tundra hard cooler onboard with ice... just bring your fav adult beverages. Highly recommend for a fun, luxe day with your besties.

35ft C&C 35 Sailboat in Toronto

It was a great experience for me and my whole family. Peter made us a part of sailing experience and my husband and our teenagers gladly participated in everything that needed to be done and also enjoyed the conversation and the company of the captain. Thank you, Peter!

Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.

What a WONDERFUL experience!! Capt. Russell was truly amazing, our 2 hour cruise Friday could not have been better! His attention to detail, coupled with a strong focus on safety didn't go unnoticed. We had 1 person in our party that was a little nervous about being on the open water. The Capt. was able to sooth their apprehension with his vast knowledge of sailing, peppered with humor...it was the needed medicine. We will be back soon, next time we'll book a 4 hour cruise, 2 hours was clearly not enough time. 5 star recommendation, only because 6 stars was not an option.

Discover Sailing 3hr Introductory Sail

It was great to have Gone Sailing with capt Howie! he was extremely knowledgeable about sailing and a patient teacher; strongly recommend and will go direct to him next time I’m in town.

35ft C&C 35 Sailboat in Toronto

I need just one word to describe this experience! - Incredible ! 🤩🤩